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Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione
In the title dithioglycoluril derivative, C(19)H(20)N(4)O(3)S(2), there is a difference in the torsion angles between the thioimidazole moiety and the methoxyphenyl groups on either side of the molecule [C—N—C(ar)—C(ar) = 116.9 (2) and −86.1 (3)°, respectively]. The N—C—N bond angle on one sid...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6727056/ https://www.ncbi.nlm.nih.gov/pubmed/31523453 http://dx.doi.org/10.1107/S2056989019010764 |
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author | Asegbeloyin, Jonnie N. Ifeanyieze, Kenechukwu J. Okpareke, Obinna C. Oyeka, Ebube E. Groutso, Tatiana V. |
author_facet | Asegbeloyin, Jonnie N. Ifeanyieze, Kenechukwu J. Okpareke, Obinna C. Oyeka, Ebube E. Groutso, Tatiana V. |
author_sort | Asegbeloyin, Jonnie N. |
collection | PubMed |
description | In the title dithioglycoluril derivative, C(19)H(20)N(4)O(3)S(2), there is a difference in the torsion angles between the thioimidazole moiety and the methoxyphenyl groups on either side of the molecule [C—N—C(ar)—C(ar) = 116.9 (2) and −86.1 (3)°, respectively]. The N—C—N bond angle on one side of the dithioglycoluril moiety is slightly smaller compared to that on the opposite side, [110.9 (2)° cf. 112.0 (2)°], probably as a result of the steric effect of the methyl group. In the crystal, N—H⋯S hydrogen bonds link adjacent molecules to form chains propagating along the c-axis direction. The chains are linked by C—H⋯S hydrogen bonds, forming layers parallel to the bc plane. The layers are then linked by C—H⋯π interactions, leading to the formation of a three-dimensional supramolecular network. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate the molecular interactions in the crystal. |
format | Online Article Text |
id | pubmed-6727056 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-67270562019-09-13 Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione Asegbeloyin, Jonnie N. Ifeanyieze, Kenechukwu J. Okpareke, Obinna C. Oyeka, Ebube E. Groutso, Tatiana V. Acta Crystallogr E Crystallogr Commun Research Communications In the title dithioglycoluril derivative, C(19)H(20)N(4)O(3)S(2), there is a difference in the torsion angles between the thioimidazole moiety and the methoxyphenyl groups on either side of the molecule [C—N—C(ar)—C(ar) = 116.9 (2) and −86.1 (3)°, respectively]. The N—C—N bond angle on one side of the dithioglycoluril moiety is slightly smaller compared to that on the opposite side, [110.9 (2)° cf. 112.0 (2)°], probably as a result of the steric effect of the methyl group. In the crystal, N—H⋯S hydrogen bonds link adjacent molecules to form chains propagating along the c-axis direction. The chains are linked by C—H⋯S hydrogen bonds, forming layers parallel to the bc plane. The layers are then linked by C—H⋯π interactions, leading to the formation of a three-dimensional supramolecular network. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate the molecular interactions in the crystal. International Union of Crystallography 2019-08-06 /pmc/articles/PMC6727056/ /pubmed/31523453 http://dx.doi.org/10.1107/S2056989019010764 Text en © Asegbeloyin et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Asegbeloyin, Jonnie N. Ifeanyieze, Kenechukwu J. Okpareke, Obinna C. Oyeka, Ebube E. Groutso, Tatiana V. Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione |
title | Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione |
title_full | Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione |
title_fullStr | Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione |
title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione |
title_short | Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione |
title_sort | crystal structure and hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1h,3h)-dithione |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6727056/ https://www.ncbi.nlm.nih.gov/pubmed/31523453 http://dx.doi.org/10.1107/S2056989019010764 |
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